dalesconol-a and 2-norbornene

Herein, we describe a concise total synthesis of dalesconol A through a "polycyclization/oxidation" approach. In the polycyclization stage, a Pd(0)/NBE-catalyzed 3-fold domino reaction and a subsequent intramolecular Michael addition have been utilized for the one-step assembly of the heptacyclic molecular skeleton. In the late stage of oxidation state adjustments, a stepwise sequence including site-selective benzylic oxidation, Pd(II)-catalyzed oxime ether directed trihydroxylation, and desaturation has been adopted to introduce the oxygen functionalities and furnish the synthesis of dalesconol A. With the advantage of the late-stage amidation of three C-H bonds in a single step, the amino analogue of dalesconol A has also been obtained with high efficiency.

Topics: Carbon; Catalysis; Crystallography, X-Ray; Hydrogen; Hydroxylation; Molecular Conformation; Norbornanes; Oxidation-Reduction; Palladium; Polycyclic Aromatic Hydrocarbons; Stereoisomerism